Windward Side Vacations from $879
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Your Windward Side Vacation
Our Windward Side vacation packages give you the power to create your own adventure. Tailor your journey to suit your needs and interests and make every moment count in this wonderful city. Make your trip to Windward Side even more fun by going sightseeing. Wells Bay Beach, Cove Bay Beach and Dutch Museum of Saba are some of the major attractions you'll want to explore. Whoever you're going away with and whatever the size of your budget, your dream Windward Side vacation is just clicks away with Expedia.
The Latest Windward Side vacation packages
Price found within the past 48 hours. Click for updated prices.
El Momo Cottages
$879
per person
Nov 11 - Nov 14
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to Saba (SAB)
8.6/10 Excellent! (61 reviews)
mosquitos you had to climb 80 slippery steps to climb to reach to tiny room they call cottage
one night strange voices of man and woman when i was told that only one or two
people lived in
mosquitoes bites whole body criquet sounds all night /cant sleep to reach toilet at
night walk down 4 to 5 slippery steps in rain
jungle like environment
i was forced to leave after staying 3 nights and flnd better hotel and pay again for rest in Saba till 13 sept
i complained to expedia customer service and they requested refund from cottabe peolple but no reply yet
Reviewed on Sep 15, 2026
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See all available trips from Columbus to Windward Side
View all tripsStay near popular Windward Side attractions
Dutch Museum of Saba
8.4/10 (5 reviews)
You can spend time browsing the exhibits at Dutch Museum of Saba in Windward Side. While you're in the area, wander around the gardens.
Harry L Johnson Museum
8.8/10 (3 reviews)
You can spend an afternoon studying the exhibits at Harry L Johnson Museum in Windward Side. While you're in the area, wander around the gardens.
Saba Heritage Center
You can spend an afternoon studying the exhibits at Saba Heritage Center in Windward Side. Wander the seaside and rainforest while you're in the area.
Jo Bean Glass Art Studio
9.8/10 (8 reviews)
You can spend an afternoon studying the exhibits at Jo Bean Glass Art Studio in Windward Side. While you're in the area, wander around the gardens.
What to do in Windward Side
Historic City, Fort and Beach E-Bike Tour
$130
per adult
100% of travellers recommend
5 Days Safari to Lake Naivasha, Hells Gate N/P, Maasai Mara N/R.
$1,150
per adult
Windward Side Hotel Deals
Saba Arawak Hotel
The peak Windward Side Saba
$143 nightly
$150 total
Sep 17 - Sep 18
Total with taxes and fees
8.4/10 Very Good! (99 reviews)
"Love the place"
Reviewed on Sep 5, 2026
The Cottage Club Hotel
17a Grey Bush Street Windward Side Saba
10/10 Exceptional! (1 review)
"Beautiful views. Very centrally located and quiet."
Reviewed on Nov 24, 2021
El Momo Cottages
Booby Hill Windward Side Saba
8.6/10 Excellent! (62 reviews)
"mosquitos you had to climb 80 slippery steps to climb to reach to tiny room they call cottage one night strange voices of man and woman when i was told that only one or two people lived in mosquitoes bites whole body criquet sounds all night /cant sleep to reach toilet at night walk down 4 to 5 slippery ..."
Reviewed on Sep 15, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find the Best Windward Side Vacation Packages
Windward Side Essential Information
Closest Airport | Juancho E. Yrausquin Airport (SAB) |
|---|---|
Population | 440 |
Max Temp Winter | 80ºF |
Max Temp Summer | 80ºF |
Top Sights | Wells Bay Beach, Cove Bay Beach and Dutch Museum of Saba |
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Frequently asked questions
How much does a Windward Side vacation package cost?
You can pick up a vacation package to this destination from $879 on Expedia. But how much your vacation to Windward Side costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Windward Side?
You can typically find lower prices and better availability in May, June and September. Take a look at our cheap Windward Side vacation packages and you could land some excellent off-season deals.
How many days is enough for Windward Side?
You can easily visit all the leading attractions in Windward Side in a few days, including the must-see Jo Bean Glass Art Studio. If you're after a longer Windward Side vacation, look at what kind of excursions and activities are available nearby.
Is it worth booking a vacation package to Windward Side?
Popular for its walking trails, underwater activities and nature, a Windward Side vacation is a hit with all kinds of travelers. Be sure to visit leading sights like Dutch Museum of Saba and Mt Scenery, and consider renting some wheels for day trips to discover even more.
How to find the best Windward Side package deals?
Use Expedia's filter tool to help you find some fabulous Windward Side package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Windward Side package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package well in advance.
Is it cheaper to book a Windward Side vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still have the flexibility to create a customized Windward Side vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Windward Side?
Land incredible bargains by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Windward Side getaway.
Does Expedia offer Book Now, Pay Later Windward Side vacation packages?
Your Windward Side break is meant to be an escape from your busy life, not a source of money worries. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.